tert-butyl (2S)-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinecarboxylate | 463962-06-3

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: tert-butyl (2S)-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinecarboxylate
• 英文别名: N-Tosyl-L-pyroglutaminsaeure-tert.-butylester, 1-Tosyl-L-pyrrolidon-(5)-carbonsaeure-(2)-tert.-butylester；(S)-tert-butyl 5-oxo-1-tosylpyrrolidine-2-carboxylate
• CAS: 463962-06-3
• 化学式: C₁₆H₂₁NO₅S
• 分子量: 339.412
• InChiKey: CXEROEHGCQFDNE-ZDUSSCGKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.02
• 重原子数：
  23.0
• 可旋转键数：
  3.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  80.75
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  tert-butyl (2S)-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinecarboxylate 在 咪唑 、 sodium tetrahydroborate 、 偶氮二异丁腈 、 碘苯二乙酸 、 碘 、 三正丁基氢锡 、 三苯基膦 作用下， 以 四氢呋喃 、 氘代氯仿 、 二氯甲烷 、 苯 为溶剂， 反应 7.5h， 生成 (S)-tert-butyl 1-tosylpyrrolidine-2-carboxylate
  参考文献：
  名称：

  Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

  摘要：

  Mechanistic evidence observed in Hofmann-Loffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity.

  DOI：

  10.1021/acs.orglett.5b00866
• 作为产物：
  描述：

  tert-butyl (2S)-5-hydroxy-2-{[(4-methylphenyl)sulfonyl]amino}pentanoate 在 咪唑 、 碘苯二乙酸 、 碘 、 sodium carbonate 、 三苯基膦 作用下， 以 氘代氯仿 、 二氯甲烷 为溶剂， 反应 77.0h， 生成 tert-butyl (2S)-1-[(4-methylphenyl)sulfonyl]-2-pyrrolidinecarboxylate
  参考文献：
  名称：

  Chemoselective Intramolecular Functionalization of Methyl Groups in Nonconstrained Molecules Promoted by N-Iodosulfonamides

  摘要：

  Mechanistic evidence observed in Hofmann-Loffler-Freytag-type reactions has been crucial to achieve the chemoselective functionalization of methyl groups under mild conditions. Radical-mediated methyl iodination and subsequent oxidative deiodination are the key steps in this functionalization, where iodine chemistry has a pivotal role on the formation of the C-N bond. The concepts of single hydrogen atom transfer (SHAT) and multiple hydrogen atom transfer (MHAT) are introduced to describe the observed chemoselectivity.

  DOI：

  10.1021/acs.orglett.5b00866

文献信息

• Remote Chiral Induction in Vinyl Sulfonium Salt-Mediated Ring Expansion of Hemiaminals into Epoxide-Fused Azepines
  作者：Muhammad Yar、Matthew G. Unthank、Eoghan M. McGarrigle、Varinder K. Aggarwal

  DOI：10.1002/asia.201000817

  日期：2011.2.1

  The planet of the azepines: Epoxy‐fused azepines have been synthesized in a highly selective reaction with hemiaminals and vinyl sulfonium salts. Stereochemistry is controlled by the substituent at the four‐ or five‐position of the hemiaminal. The key step involves ring‐opening of the hemiaminal, conjugate addition onto a vinyl sulfonium salt, and epoxidation of the aldehyde by the in situ formed sulfur

  ze庚烷的星球：环氧稠合的ze庚烷是通过与hemiaminals和乙烯基sulf盐的高度选择性反应而合成的。立体化学是由半胱氨酸的4位或5位上的取代基控制的。关键步骤包括打开半胱氨酸开环，将共轭物加到乙烯基sulf盐上，以及通过原位形成的硫叶立德将醛环氧化。
• Taschner,E. et al., Justus Liebigs Annalen der Chemie, 1961, vol. 646, p. 127 - 133
  作者：Taschner,E. et al.

  DOI：——

  日期：——